DE2903717A1 - Verfahren zur herstellung einer waessrigen aufschlaemmung einer wasserunloeslichen azoverbindung - Google Patents
Verfahren zur herstellung einer waessrigen aufschlaemmung einer wasserunloeslichen azoverbindungInfo
- Publication number
- DE2903717A1 DE2903717A1 DE19792903717 DE2903717A DE2903717A1 DE 2903717 A1 DE2903717 A1 DE 2903717A1 DE 19792903717 DE19792903717 DE 19792903717 DE 2903717 A DE2903717 A DE 2903717A DE 2903717 A1 DE2903717 A1 DE 2903717A1
- Authority
- DE
- Germany
- Prior art keywords
- stream
- water
- coupling
- sulfuric acid
- azo compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 azo compound Chemical class 0.000 title claims description 44
- 239000002002 slurry Substances 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 59
- 238000005859 coupling reaction Methods 0.000 claims description 58
- 238000010168 coupling process Methods 0.000 claims description 51
- 230000008878 coupling Effects 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 238000002156 mixing Methods 0.000 claims description 31
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 28
- 239000012528 membrane Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 150000001989 diazonium salts Chemical class 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 238000006193 diazotization reaction Methods 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 43
- 239000000047 product Substances 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 21
- 239000000975 dye Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- 239000004094 surface-active agent Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000012954 diazonium Substances 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000108 ultra-filtration Methods 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 10
- 239000000376 reactant Substances 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 5
- 239000000987 azo dye Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- JCXUJLWOJLTKRV-UHFFFAOYSA-N 2-methoxyethyl 3-(5-acetamido-2-methoxyanilino)propanoate Chemical compound COCCOC(=O)CCNC1=CC(NC(C)=O)=CC=C1OC JCXUJLWOJLTKRV-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000000909 electrodialysis Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FVNSRFMQXKMHTQ-UHFFFAOYSA-N (2-amino-1,3-benzothiazol-6-yl) thiocyanate Chemical compound C1=C(SC#N)C=C2SC(N)=NC2=C1 FVNSRFMQXKMHTQ-UHFFFAOYSA-N 0.000 description 2
- 150000005003 1-naphthylamines Chemical class 0.000 description 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 2
- 150000004793 2,6-dihydroxypyridines Chemical class 0.000 description 2
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000005189 flocculation Methods 0.000 description 2
- 230000016615 flocculation Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- XUBDTGBUGMAAHD-UHFFFAOYSA-N methyl 3-(5-acetamido-2-methoxy-n-(3-methoxy-3-oxopropyl)anilino)propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)C1=CC(NC(C)=O)=CC=C1OC XUBDTGBUGMAAHD-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- PUYOZGLXKYWMBT-UHFFFAOYSA-N 1-(4-methoxyphenyl)pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1N1N=C(N)C=C1 PUYOZGLXKYWMBT-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 description 1
- PJCAOXWCMOVGQL-UHFFFAOYSA-N 2-[5-acetamido-n-(2-acetyloxyethyl)-2-ethoxyanilino]ethyl acetate Chemical compound CCOC1=CC=C(NC(C)=O)C=C1N(CCOC(C)=O)CCOC(C)=O PJCAOXWCMOVGQL-UHFFFAOYSA-N 0.000 description 1
- AEQXCNSBJJHGGE-UHFFFAOYSA-N 2-[5-acetamido-n-(2-acetyloxyethyl)-2-methoxyanilino]ethyl acetate Chemical compound COC1=CC=C(NC(C)=O)C=C1N(CCOC(C)=O)CCOC(C)=O AEQXCNSBJJHGGE-UHFFFAOYSA-N 0.000 description 1
- GDFCZZHSWGWCHP-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-6-carbonitrile Chemical compound C1=C(C#N)C=C2SC(N)=NC2=C1 GDFCZZHSWGWCHP-UHFFFAOYSA-N 0.000 description 1
- YJTBHWXNEMGNDC-UHFFFAOYSA-N 2-amino-1,3-thiazole-5-carbonitrile Chemical compound NC1=NC=C(C#N)S1 YJTBHWXNEMGNDC-UHFFFAOYSA-N 0.000 description 1
- RIYSFSQPHCAGLS-UHFFFAOYSA-N 2-amino-3,5-dinitrobenzonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O RIYSFSQPHCAGLS-UHFFFAOYSA-N 0.000 description 1
- MUHLVSZIVTURCZ-UHFFFAOYSA-N 2-amino-3-bromo-5-nitrobenzonitrile Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1C#N MUHLVSZIVTURCZ-UHFFFAOYSA-N 0.000 description 1
- XVYNBLCPQVDRCH-UHFFFAOYSA-N 2-amino-3-chloro-5-nitrobenzonitrile Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1C#N XVYNBLCPQVDRCH-UHFFFAOYSA-N 0.000 description 1
- OEYPRQITPHCATA-UHFFFAOYSA-N 2-amino-3-methyl-5-nitrobenzonitrile Chemical compound CC1=CC([N+]([O-])=O)=CC(C#N)=C1N OEYPRQITPHCATA-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- ZBEGDHIBRPHOBV-UHFFFAOYSA-N 2-amino-5-nitrobenzene-1,3-dicarbonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1C#N ZBEGDHIBRPHOBV-UHFFFAOYSA-N 0.000 description 1
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- GLUCALKKMFBJEB-UHFFFAOYSA-N 2-bromo-6-chloro-4-nitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Br GLUCALKKMFBJEB-UHFFFAOYSA-N 0.000 description 1
- LHRIICYSGQGXSX-UHFFFAOYSA-N 2-chloro-4,6-dinitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O LHRIICYSGQGXSX-UHFFFAOYSA-N 0.000 description 1
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
- JANKXSWDUFKJEY-UHFFFAOYSA-N 2-methoxyethyl 3-(5-acetamido-n-ethyl-2-methoxyanilino)propanoate Chemical compound COCCOC(=O)CCN(CC)C1=CC(NC(C)=O)=CC=C1OC JANKXSWDUFKJEY-UHFFFAOYSA-N 0.000 description 1
- OZDKQEYDVKOALG-UHFFFAOYSA-N 2-methyl-5,7-dinitroindazol-3-amine Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC2=C(N)N(C)N=C21 OZDKQEYDVKOALG-UHFFFAOYSA-N 0.000 description 1
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical compound NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 description 1
- SVNCRRZKBNSMIV-UHFFFAOYSA-N 3-Aminoquinoline Chemical compound C1=CC=CC2=CC(N)=CN=C21 SVNCRRZKBNSMIV-UHFFFAOYSA-N 0.000 description 1
- IBANRDPEOYZVGW-UHFFFAOYSA-N 3-methyl-1,2,4-thiadiazole Chemical compound CC=1N=CSN=1 IBANRDPEOYZVGW-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- XSFKCGABINPZRK-UHFFFAOYSA-N 4-aminopyrazol-3-one Chemical compound NC1=CN=NC1=O XSFKCGABINPZRK-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- OUQMXTJYCAJLGO-UHFFFAOYSA-N 4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(N)=N1 OUQMXTJYCAJLGO-UHFFFAOYSA-N 0.000 description 1
- NDWBXTNRCBNGAK-UHFFFAOYSA-N 4-methyl-5-nitro-1,3-thiazol-2-amine Chemical compound CC=1N=C(N)SC=1[N+]([O-])=O NDWBXTNRCBNGAK-UHFFFAOYSA-N 0.000 description 1
- PYSJLPAOBIGQPK-UHFFFAOYSA-N 4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1 PYSJLPAOBIGQPK-UHFFFAOYSA-N 0.000 description 1
- YEUFRAFORHUMLC-UHFFFAOYSA-N 5-methylsulfonyl-1,3-thiazol-2-amine Chemical compound CS(=O)(=O)C1=CN=C(N)S1 YEUFRAFORHUMLC-UHFFFAOYSA-N 0.000 description 1
- VVVCJCRUFSIVHI-UHFFFAOYSA-N 5-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=CN=CS1 VVVCJCRUFSIVHI-UHFFFAOYSA-N 0.000 description 1
- UHZHEOAEJRHUBW-UHFFFAOYSA-N 5-phenyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=CC=C1 UHZHEOAEJRHUBW-UHFFFAOYSA-N 0.000 description 1
- ZYHNHJAMVNINSY-UHFFFAOYSA-N 6-methylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 ZYHNHJAMVNINSY-UHFFFAOYSA-N 0.000 description 1
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 1
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- ABDMQSFNJPYOLA-UHFFFAOYSA-N NS(=O)(=O)[N+]([O-])=O Chemical class NS(=O)(=O)[N+]([O-])=O ABDMQSFNJPYOLA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002359 Tetronic® Polymers 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- VYJSGJXWKSDUSG-UHFFFAOYSA-N ethyl 2-amino-1,3-benzothiazole-6-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=C(N)SC2=C1 VYJSGJXWKSDUSG-UHFFFAOYSA-N 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical class OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000003854 isothiazoles Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000013627 low molecular weight specie Substances 0.000 description 1
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NQMXUYSFHRWLLV-UHFFFAOYSA-N methyl 3-(n-(3-methoxy-3-oxopropyl)anilino)propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)C1=CC=CC=C1 NQMXUYSFHRWLLV-UHFFFAOYSA-N 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- VIACAIAQHPLINF-UHFFFAOYSA-N n-benzyl-n-ethyl-3-methylaniline Chemical compound C=1C=CC(C)=CC=1N(CC)CC1=CC=CC=C1 VIACAIAQHPLINF-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/006—Special methods of performing the coupling reaction characterised by process features
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
- C09B41/005—Special methods of performing the coupling reaction characterised by the coupling medium containing low molecular weight dispersing agents; containing surface active polythylene gylcols
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S534/00—Organic compounds -- part of the class 532-570 series
- Y10S534/07—Automatic and/or continuous temperature control in the preparation of azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB581878 | 1978-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2903717A1 true DE2903717A1 (de) | 1979-08-16 |
Family
ID=9803181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792903717 Withdrawn DE2903717A1 (de) | 1978-02-14 | 1979-01-31 | Verfahren zur herstellung einer waessrigen aufschlaemmung einer wasserunloeslichen azoverbindung |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4252718A (OSRAM) |
| JP (1) | JPS54120636A (OSRAM) |
| BE (1) | BE874077A (OSRAM) |
| CH (1) | CH637982A5 (OSRAM) |
| DD (1) | DD142047A5 (OSRAM) |
| DE (1) | DE2903717A1 (OSRAM) |
| ES (1) | ES477705A1 (OSRAM) |
| FR (1) | FR2416924A1 (OSRAM) |
| GB (1) | GB2021132B (OSRAM) |
| IT (1) | IT1110291B (OSRAM) |
| PL (1) | PL213342A1 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2129434B (en) * | 1982-10-08 | 1986-04-16 | Ciba Geigy Ag | Production of azo compounds |
| CH655125A5 (de) * | 1983-09-21 | 1986-03-27 | Ciba Geigy Ag | Verfahren zur herstellung von azofarbstoffpraeparaten. |
| CH660494B (OSRAM) * | 1984-12-12 | 1987-04-30 | ||
| TW233304B (OSRAM) * | 1992-04-02 | 1994-11-01 | Hoechst Mitsubishi Kasei | |
| DE4447593C2 (de) | 1994-10-05 | 2000-12-07 | Clariant Gmbh | Toner für elektrophotographische Entwickler, enthaltend ein Azogelbpigment |
| DE69910539T2 (de) * | 1998-01-29 | 2004-06-24 | Cabot Corp., Boston | Verfahren zur reinigung einer dispersion und herstellung von inkjet tinten |
| US6346361B1 (en) * | 1999-10-06 | 2002-02-12 | Clariant Finance (Bvi) Limited | Method for synthesizing polymeric AZO dyes |
| DE102004019560A1 (de) * | 2004-04-22 | 2005-11-10 | Clariant Gmbh | Hochreine Naphthol AS-Pigmente |
| DE102004019561A1 (de) * | 2004-04-22 | 2005-11-10 | Clariant Gmbh | Verfahren zur Herstellung hochreiner Azofarbmittel |
| GB0416256D0 (en) * | 2004-07-20 | 2004-08-25 | Avecia Ltd | Manufacturing process |
| CN101054473B (zh) * | 2006-04-10 | 2010-10-20 | 浙江龙盛集团股份有限公司 | 一种耦合生产设备及生产工艺 |
| CN104830089B (zh) * | 2015-04-29 | 2017-04-19 | 绍兴文理学院 | 一种染料连续偶合及减少能耗的方法 |
| CN113634216B (zh) * | 2021-08-26 | 2022-05-31 | 大连理工大学 | 一种在管路式反应器中连续重氮化连续偶合生产水溶性偶氮染料的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD77985A (OSRAM) * | ||||
| CA572950A (en) * | 1959-03-24 | General Aniline And Film Corporation | Production of azoic pigments | |
| US2478767A (en) * | 1945-10-04 | 1949-08-09 | Du Pont | Manufacture of azo compounds |
| DE1231251B (de) * | 1963-11-28 | 1966-12-29 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Diazoverbindungen |
| DE1934388B2 (de) * | 1969-07-07 | 1975-01-16 | Vyzkumny Ustav Organickych Syntez, Pardubice-Rybitvi (Tschechoslowakei) | Verfahren zur wiederholten Chargenherstellung von Azofarbstoffen |
| US3793305A (en) * | 1970-09-14 | 1974-02-19 | Du Pont | One-step process of preparing azo dyes by simultaneous diazotization |
| US4018751A (en) * | 1975-04-09 | 1977-04-19 | American Cyanamid Company | Continuous process for aminoazobenzene |
| US4159264A (en) * | 1975-08-09 | 1979-06-26 | Ciba-Geigy Corporation | Automatic control of azo coupling processes in the manufacture of azo pigments |
-
1979
- 1979-01-31 DE DE19792903717 patent/DE2903717A1/de not_active Withdrawn
- 1979-01-31 GB GB7903441A patent/GB2021132B/en not_active Expired
- 1979-02-05 IT IT19904/79A patent/IT1110291B/it active
- 1979-02-09 BE BE0/193387A patent/BE874077A/xx not_active IP Right Cessation
- 1979-02-09 US US06/011,049 patent/US4252718A/en not_active Expired - Lifetime
- 1979-02-10 PL PL21334279A patent/PL213342A1/xx unknown
- 1979-02-13 FR FR7903607A patent/FR2416924A1/fr active Granted
- 1979-02-13 DD DD79211009A patent/DD142047A5/de unknown
- 1979-02-13 CH CH136479A patent/CH637982A5/de not_active IP Right Cessation
- 1979-02-14 ES ES477705A patent/ES477705A1/es not_active Expired
- 1979-02-14 JP JP1512779A patent/JPS54120636A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH637982A5 (de) | 1983-08-31 |
| ES477705A1 (es) | 1979-10-16 |
| US4252718A (en) | 1981-02-24 |
| GB2021132B (en) | 1982-07-21 |
| BE874077A (fr) | 1979-08-09 |
| GB2021132A (en) | 1979-11-28 |
| FR2416924B1 (OSRAM) | 1983-07-22 |
| PL213342A1 (pl) | 1979-10-22 |
| IT7919904A0 (it) | 1979-02-05 |
| JPS54120636A (en) | 1979-09-19 |
| DD142047A5 (de) | 1980-06-04 |
| FR2416924A1 (fr) | 1979-09-07 |
| IT1110291B (it) | 1985-12-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |